


Tahitian Twilight - A “What If" Story

by Whos the Boss_Geekery (Outlander_Geekery)



Category: Who's the Boss?
Genre: F/M
Language: English
Status: Completed
Published: 2020-12-31
Updated: 2020-12-31
Packaged: 2021-03-10 23:47:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,672
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28461903
Author URL: https://archiveofourown.org/users/Outlander_Geekery/pseuds/Whos%20the%20Boss_Geekery
Summary: What if Angela and Tony had started a relationship the night of Samantha’s prom.  This is the evening where Tony recreated Angela's prom night in the tag of the episode. It's in my top 5 romantic moments between them, and honestly, the latest point in the series to me that seems realistic for them to get together. By this episode, Angela had admitted to herself that she is in love with Tony, and Tony had to be in love with her to make such a romantic gesture. I decided to  let them have a little play time.
Relationships: Angela Bower/Tony Micelli
Comments: 3
Kudos: 12





	Tahitian Twilight - A “What If" Story

“Tony, if we don’t stop we’re going to end up having sex on this couch.”

Tony almost couldn’t believe those words just came out of Angela’s mouth, but based on their current situation, she was right. 

The evening had started out innocently enough. Tony had had romance on his mind, but their brand of romance — some flirting, some dancing, maybe even a kiss they wouldn’t talk about later. This was something he’d not imagined. 

Once Samantha and Jessie left for prom, and Jonathan announced he was sleeping at Peter’s, they’d had the house to themselves. Angela asked if he wanted to watch a movie, but Tony had other plans. He encouraged Angela to go relax in a nice hot bath since she had spent most of the afternoon running around the city. As soon as he heard the water running he got to work. By the time he went to her room to coax her back downstairs, the living room was a virtual wonderland of palm trees and charm. 

He had recreated her prom night. 

“You are so sweet.” She’d said it with so much tenderness and warmth in her eyes that it made his stomach flip. He may not be as rich, or as educated as the men she normally dated, but he knew how to woo a woman, especially when he was head over heels in love with that woman. 

They’d danced and laughed and sipped on champagne. It’d only taken him one glass to get the courage to kiss her. 

During a slow dance, he nuzzled his face into her neck and inhaled deeply. When she didn’t pull away, and even gave a soft sigh, he knew he was free to make a move. He brought his face to hers and gently rubbed his nose from side to side against hers. She smiled at the gesture. He moved in, hovering just long enough to give her the opportunity to pull away before their mouths met. 

She didn’t pull away. She kissed him. Boy, did she kiss him. 

The next thing Tony knew he had his hands in her hair and his tongue in her mouth. She tasted like champagne and smelled so sweet. Her lips were just as soft as he remembered from their few other kisses. None of them had ever lasted this long, however. 

Angela wrapped her arms around Tony’s waist and pulled him in closer. He’d felt some stirring as soon as they started dancing so within seconds of their lips touching he’d become embarrassingly hard. There was no way she didn’t notice now that she had brought their hips together. Tony knew the gentlemanly thing to do would be to put a little space between them, but he wasn’t feeling particularly gentlemanly in the moment. He was just feeling. Feeling Angela and loving it. She alternated between gently capturing his bottom lip between her own and darting her tongue out to meet his only to slip away, encouraging him to seek her out again. He slid his own hands down and cupped her rear, bringing her even closer. 

She pulled away and he was about to apologize when Angela took his hand and led him to the couch. They were kissing again before either of them were even fully seated. He couldn’t get enough of her. 

Her hands roamed through his hair as she gently pulled him to lie next to her on the narrow couch. Tony excitedly grabbed the small pillows off the couch and threw them to the floor to make more room for her. This was their living room couch. He was making out with her in the middle of their home. Being completely consumed with kissing Angela, he couldn’t remember if Mona had told him her plans for the night. He hoped she wouldn’t be making an entrance anytime soon, or at all.

The thought left his head as Angela’s hand made its way down to his rear and pulled him tighter against her body. Tony’s erection pressed into her thigh and Angela inhaled deeply before softly moaning her approval into his mouth. 

As she pushed her hips into his, Tony couldn’t help but try to get even closer to her. He slid his hand down to the tie of her robe and pulled. When he didn’t get any resistance, he slid his hand inside and reached around to cup her rear in his hand. He kneaded the soft round globe of one of her cheeks before pinching the silky fabric covering it so he could pull up her nightgown.

Their mouths never left each other as Angela lifted her hips slightly to let him slide her gown up enough so he could run his hand back to her backside and under the delicate stitching of her panties where her thigh ended and her butt began. Tony’s heart skipped a beat every time he thought about the fact that he was touching Angela’s bare skin in such an intimate spot. No matter how this night ended, they could never again truly say they hadn’t been intimate. 

Busy with his exploration of this uncharted part of Angela, he almost didn’t realize that she was exploring as well. The hand that wasn’t sandwiched between them was under his sweater and gently caressing the soft hairs at the center of his chest. He felt her fingertips explore his nipples and wondered if she was giving him a hint. To test his theory, he slid the hand that had been exploring her rear north. She gasped into his mouth when he fully cupped her breast. 

He slipped her robe and nightgown strap down just enough to scoop a breast out. He’d had a vision of her breasts in his head ever since the day he had accidentally caught her naked. Now he was holding her in his hand -- all soft and warm, and just as pink and tan and he remembered. He went in for a kiss, but this time on her pebbled nipple instead of her lips. 

“Tony, if we don’t stop we’re going to end up having sex on this couch.”

And that’s how they had gotten here -- with Angela suggesting that this would end with sex.

“Would it be the end,” he paused to kiss a tight bud, “or the beginning?” He tore himself away from her breast to look her in the eyes. 

“What do you mean?” Angela asked breathlessly.

“Is that all it would be, sex?” The conversation had halted his exploration a bit, but Tony still let his thumb lightly caress her nipple while they sorted this out. He wanted to make sure she knew what she’d be giving up if she turned him down. Her nipple was still tight under his touch. He had at least this part of her on his side. 

“What do you want it to be?” Angela ran her fingers through his hair as she posed the question.

“Angela, it’s obvious that I’m attracted to you.” Tony nodded his head in the direction of where his obvious attraction was prodding her thigh. “But, I think it’s also obvious I have feelings for you beyond attraction.” He nodded his head in the direction of the decorated living room.

“This is the most romantic thing any man has ever done for me.” Angela’s gaze followed his nod to the makeshift prom setting. 

His hand left her breast to caress her cheek. “Well, you know, what you did for Sam today was one of the most thoughtful things anyone has ever done for her.”

“Oh.” Angela replied. 

Tony quickly added, “But, that’s not why I did this, if that’s what you're thinking. I already had this planned after Mona told me about big-ears Bigalow.” He pulled her in closer. “I did this because you deserve only the best things in life, and I wanted to make a memory with you that would overshadow any dumb thing some jerk did to you in high school.”

“It worked. This is a night I will never forget for a few reasons.” Angela captured his lips again. 

Tony had more to say, but anytime Angela’s lips were on his, he forgot about everything else but continuing to touch her. He was throbbing with arousal and he had a feeling if he reached between her legs he would find her just as worked up.

As Angela’s hand found its way to the front of Tony’s pants he realized he had to get a clear head and quick. 

He gently took her hand in his and brought it to his lips. “But, I meant it when I said you deserve only the best things in life. I want to be with you, but I want to make sure you understand what being with me means. I’m never going to be able to give you some of the things you deserve. I’m going back to school, and I’m not going to be your housekeeper forever, but even after I graduate and find another job, the reality is you will probably always make significantly more than I do. Are you okay with that? Like really okay with that? Because we’d be risking a lot to take this chance.”

“I’m sure. I’ve been sure for a while now, but I was scared you may not feel the same way. I don’t care how much money you make. You are the most loving, thoughtful, and sensitive man I have ever known. Other men can’t compete with you.”

“Angela, we’re talking trading in Chez Rene for Pizza Playland, the country club for Bongo Burger--”

Angela laughed, “Tony, stop. I love pizza, I love burgers, and your cooking is better than Chez Rene and the country club. But who says the man has to always pay? Sounds pretty sexist if you ask me. We’re partners and we always have been. That will never change.”

Angela kissed him again before adding in a soft tone, “The kids won’t be back until morning, come to bed with me.”

Tony was surprised by her boldness. The majority of his body wanted to say yes, but he shook his head. “Not tonight. Not like this. You haven’t even taken me out on a date yet.”

Angela cupped his face and kissed him. He grabbed her rear again and pulled her to him. They were both torturing themselves, but it felt so damn good.

Tony hiked her leg up over his under her robe and ran his fingers along her seam. He could feel how hot and wet she was through her panties. God help him, she was so ready for him.

“I don’t want to send you to bed alone like this.” Tony whispered into her mouth. 

“Then don’t.” He knew she was asking him to take her to bed again, but he couldn’t. But he could still not send her to bed frustrated..

Tony reached for the waistband of her panties and tugged. He felt her hips shift to help him along and they worked together quickly to kick them off her legs, taking her bunny slippers with them. He wasted no time bringing his hand back to her center. Wet. Hot. It was all his brain could compute in the moment. She felt amazing and Tony took a deep breath to get himself under control so he didn’t just give in, unzip and slide into her. 

Angela nudged against his hand and Tony came back to himself. She wanted him and he loved her too much to deny her. 

He dipped his fingers into her wetness before slipping over the little tight knot above her opening. She moaned and bit at his bottom lip. He was touching her. It wasn’t intercourse, but this was definitely sex. They were having sex. 

“Angela…” He sighed into her mouth. There was so much more he wanted to say but right now he could only speak with actions. 

“Please, Tony… more.”

He slid a finger deep inside of her and she cried out. He felt for the soft patch of heat he hoped he’d find. He didn’t know Angela well enough to know if this would work, but she was turned on enough for him to try. He loved this part of being with a woman, learning her body and what made her unique. The fact that it was Angela and he was in love with her made it even better. He’d wondered so often what would make her squirm, what would make her come. 

She whimpered as he rubbed. The sounds of his finger working inside of her and her little moans in his mouth almost made him come undone. She was moving her hips in small pulses, like she couldn’t keep still, pushing down as he wiggled inside to increase the pressure. Her hands gripped the collar of his sweatshirt as if she would float away if she wasn’t holding on to him. A distant part of his brain that wasn’t completely consumed with arousal, thought about how much he liked this sweatshirt and if she was going to stretch out the collar. Eh, it was worth it. 

Her constant moans made it hard for them to land a full kiss, but she licked and nipped at his open lips between pants. The rhythm of her hips increased and he took her lead. She was close. The mildly crude and incredibly turned on part of his brain was high fiving himself over the fact that he was about to make Angela come in his arms.

One hand left his collar and slid down to grasp him through his pants. If Angela hadn’t been so caught up in her own pleasure, and had any focused pressure or rhythm to her hold on him, he would have been in serious danger of embarrassing himself. That hadn’t happened to him since he was 14 and Constance Napoli let him dry hump her. 

His thoughts were interrupted by Angela crying out and pulling on his sweatshirt with even more force. He felt her insides clamp down around his fingers before her body released in sucking pulses. She shuddered in his arms. 

As she came down from her orgasm, Tony continued to nip at her lips while gently still fingering her through the aftershocks.

“Woah.” It wasn’t the most romantic thing he could have said, but it was all he could manage at the moment.

Angela took a few more deep breaths as she got her breathing back under control. “Yeah.”

Tony slipped his hand from between her legs and gripped her rear again to pull her against him in a hug, slipping his thigh between her legs to get as close to her as possible. 

“Wo-ooo-ah.” Tony was obnoxiously proud of himself.

Angela smiled and rolled her eyes. “Don’t get too full of yourself, Casanova. That was a long time coming. Oh!” Angela clapped a hand over her mouth as soon as she realized the double entendre. 

They both giggled.

“You know what I mean!” Angela looked away. “It may not always be quite that easy.” She buried her face in his neck and kissed it.

“I know. I’m just excited I could excite you so much.” Tony kissed her forehead. 

“Tony, I care deeply for you so this wasn’t just excitement. It was ... a lot of feelings finally being expressed.” 

“I *love* you, Angela. I wouldn’t have done this if I didn’t. We have too much to lose.”

She looked him in the eye. “I love you, too.”

Tony took her hand in his and interlaced their fingers, “You know, I may not be able to give you everything you deserve, but I will always put your needs before my own.” Tony smiled at her, “And not just in the bedroom.”

Angela gave a coy smile and said, “Your turn.”

She reached for his zipper. 

“No, it’s okay. I’ll make a mess.” Tony reached for her hand.

Angela looked into his eyes before giving him a sweet peck on the lips. “No you won’t.”

Did she mean?

Angela untangled their legs and slid down his body. She undid his button and slid the zipper down. She tugged him back to a seating position and slipped off the couch to kneel in front of him.

“Really, you don’t have to…” 

He would never be able to vacuum, or dust, or even sit in this room without getting a hard on at the thought of what was about to happen. He hadn’t even considered this would be on the menu this soon.

He felt his pants and underwear slip to his thighs. He didn’t remember lifting his hips to help her. 

He really should stop her, right? The thing was, though, he didn’t want her to stop, and if he said anything else she may question why he was stopping her. It was really just the gentlemanly thing to do at this point to stay quiet--

“Oh, God.” He slammed his eyes shut as his head fell back onto the couch. He was in her mouth.

Wet. Hot. Again his brain was only half functioning. 

She hummed her approval and gently sucked as her mouth slipped him out all the way to the tip before eagerly taking him back inside. 

Tony had had a feeling Angela would be good in bed. As proper and naive as she appeared to be, he saw the fire in her eyes. She’d teased him the morning after their first kiss that she would leave an impression on him if they ever had sex and she wasn’t kidding. Tony was impressed. It didn’t have anything to do with skill, although he had no complaints so far, but it was that she was truly enjoying herself. She wanted to do this for him. She wanted him to feel good. He felt amazing and it wasn’t just sexual -- he loved her so much and for her to want him as much as he wanted her made him feel invincible. 

He looked down and gently swept her hair out of her face so he could see her. She had her hand wrapped around his base and her lips around the rest. She alternated between slow and fast movements, leisurely letting him enjoy the feel of her tongue glide his entire length before swirling the sensitive tip, and sinking back down. On one gentle tug of her lips, she looked up at him to make eye contact and smiled at him somehow with just her eyes. 

He wanted to call her baby. He wanted to tell her that her mouth felt so fucking hot and she was going to make him come. But this was Angela and he didn’t really know where she stood yet on a little dirty talk. Instead he decided to tell her what his heart was feeling. “Oh, it feels so good. You’re so beautiful, Angela. I can’t believe this is actually happening. Ohhh… Ohhh…”

How did they get here tonight? As he’d been setting up fake palm trees, never in his wildest dreams did he think they could end up like this. Technically, she was still his boss, and his boss was on her knees right now—

He felt the telltale burn start deep in his groin and knew he was nearing the end. Later, he’d have to contemplate why it was that thought that pushed him to the edge.

“Angela,” he said through pants, “I’m assuming since you said what you said, that you don’t mind what’s about to happen, happening, where it’s going to happen, but if I’m wrong I just want to warn you because it’s about to happen really soon…”

Angela’s only response was to double down on her efforts. 

“Fuuuck…. Oh, Angela. Ohh.. Ohhh.” Tony gripped her arms, and curled forward around her as pleasure washed over him. 

He let his breathing slow and gave her a moment before he pulled her back into his lap for a hug.

“Do you ever stop talking?” Angela smiled at him.

“Maybe next time I should be the one with my mouth occupied.” Tony waggled his eyebrows at her.

A red blush tinted Angela’s cheeks at the suggestion. “Come to bed with me.”

“I still think we should wait.” Tony ran a finger down the soft lapel of Angela’s robe. 

“We will. We took the edge off. I just want to be with you for a bit.”

“I’ll be begging you for more in about twenty minutes.” 

“You wouldn’t have to beg.” She kissed him. “But no, we should wait. We can wait. But come to bed with me.”

“What if we fall asleep? I don’t want to risk getting caught.”

“I’ll set an alarm. Sam won’t be home until at least 5:30.”

Tony still looked unsure.

“Tony, we just had an incredibly intimate experience, and I would really like to not have to say goodnight to you in the hallway. I want to sleep in your arms, at least for a little while.”

“Okay.” There was really no way he could deny her that. He wanted the same thing. 

“Yeah?” 

“Yeah. We’ll set an alarm. I just don’t want to get caught. I don’t want the kids to find out about us this way.”

“We won’t. They won’t. I’ll set the alarm for 4:30, just in case. And I’ll get up and make sure no one is home yet first.”

Tony licked his lips and kissed her. 

Angela took his hand and stood up to pull him off the couch. Tony pulled up his underwear and pants with a slight blush, not bothering to refasten anything. They quickly looked around to gather Angela’s discarded panties and slippers. She slipped her feet into the slippers and her panties into her robe pocket.

“Come on,” Angela tugged on his hand. “We can deal with the rest in the morning. Let’s get some sleep. Tomorrow night you’re taking me to Bongo Burger -- now I’m craving their bacon burger and a milkshake.”

“You got it, baby.”

They headed upstairs to bed.

**Author's Note:**

> Thank you for reading! And thank you to all the writers still writing for Who's the Boss!
> 
> I don't have a proof reader so please feel free to let me know about any typos and I will fix them. Happy New Year!


End file.
